Nitric Acid → 6-Nitrobenzothiazole

HRID 1699965Notes

Reaction equation

HRID 1699965 reaction equation
C[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[N+:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[CH:2][S:3][C:4]=2[CH:10]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 84462-Methylbenzothiazole2×

Product 1

HCID 762566-Nitrobenzothiazole

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

Nitration of 2-methylbenzothiazole was performed following the method of Mizuno (1952) J. Pharm. Soc. Japan 72:745. A mixture of fuming nitric acid (1.6 mL) and concentrated sulfuric acid (1.2 mL) was added to an ice-cooled solution of 2-methylbenzothiazole (2 g) in sulfuric acid (8 mL). The resulting solution was allowed to warm to room temperature for one hour, then poured onto 100 mL of ice. The resulting solid was filtered, washed with water, and recrystallized from ethanol (80 mL) to provide 2.5 g of 6-nitrobenzothiazole (1) in the form of yellowish needles.

Workup

  1. filtrationThe resulting solid was filtered
  2. washwashed with water
  3. customrecrystallized from ethanol (80 mL)

Sources & evidence

ORD record
ord-e304326d9a804f019592358aed5b7e7e
Source dataset
uspto-grants-2002_02
Patent number
US06348596B1

Reaction notes

Loading…